N-Methyltryptamine

N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.

N-Methyltryptamine

Clinical data
Other names	NMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152
Routes of administration	Smoking, oral (with an MAOITooltip monoamine oxidase inhibitor)[1][2][3]
Drug class	Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	US: Schedule I (isomer of AMT)
Pharmacokinetic data
Duration of action	Seconds to minutes[1][2][3]
Identifiers
IUPAC name 2-(1H-indol-3-yl)-N-methylethan-1-amine
CAS Number	61-49-4 Y
PubChem CID	6088
ChemSpider	5863 Y
UNII	6FRL4L3Z7V
KEGG	C06213 Y
ChEBI	CHEBI:28136 Y
ChEMBL	ChEMBL348588 Y
CompTox Dashboard (EPA)	DTXSID70209846
ECHA InfoCard	100.000.462
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image
Melting point	87 to 89 °C (189 to 192 °F)
SMILES CNCCc1c[nH]c2ccccc12
InChI InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3 Y Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N Y
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It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase.^[4][5] It is a known component in human urine.^[6] NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).^[7]

NMT acts as a serotonin receptor agonist and serotonin releasing agent^[8] and is said to produce hallucinogenic effects in humans.^[1][2][3]

Use and effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.^[9]

According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided.^[10] On the other hand, according to Alexander Shulgin and others, NMT is active via non-oral routes.^[1][2][3] It has been said to produce psychedelic effects at doses of 50 to 120 mg by smoking or vaporization, with a duration of seconds to minutes.^[1][2][3] Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects.^[1][2][3]

NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI).^[2][3]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

NMT is known to act as a potent serotonin 5-HT_2A receptor full agonist (EC₅₀Tooltip half-maximal effective concentration = 50.7 nM; E_maxTooltip maximal efficacy = 96%).^[8] It has been reported to be inactive in activating the β-arrestin pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT_2A receptor.^[8] The drug is not an agonist of the serotonin 5-HT_1A receptor.^[8]

In addition to its serotonin 5-HT_2A receptor agonism, NMT is a potent serotonin releasing agent (EC₅₀ = 22.4 nM).^[8] It also releases dopamine and norepinephrine much more weakly (EC₅₀ = 321 nM and 733 nM, respectively; 14- and 33-fold less than for serotonin, respectively).^[8]

Society and culture

Legal status

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT).^[11]

See also

• Substituted tryptamine
• N-Ethyltryptamine (NET)
• N,N,-Dimethyltryptamine (DMT)
• Acacia confusa (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007)
• Acacia obtusifolia (NMT up to 2/3 alkaloid content)
• Acacia simplicifolia (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet et al. 1976)
• Desmanthus illinoensis (NMT major component seasonally)